, Volume 23, Issue 2, pp 253–261 | Cite as

Dehydration of the off-flavor chemical 2-methylisoborneol by the R-limonene-degrading bacteria Pseudomonas sp. strain 19-rlim and Sphingomonas sp. strain BIR2-rlima

Original Paper


The terpene 2-methylisoborneol (MIB), a major cause of off-flavor in farm-raised catfish and drinking water, is transformed by various different terpene-degrading bacteria. Two of these, the R-limonene-degrading strains Pseudomonas sp. 19-rlim and Sphingomonas sp. BIR2-rlima, dehydrated MIB with the formation of odorless metabolites 2-methylenebornane and 4-methylcamphene. These metabolites which have a structural resemblance to camphor, could be further transformed by camphor-degrading bacteria to more oxidized products. The bacterial dehydrations demonstrated here may have application in removing MIB where it is a problem.


2-Methylisoborneol Dehydration R-limonene Pseudomonas Sphingomonas Biotransformation 


  1. Altschul SF, Gish W, Miller W, Meyers EW, Lipman DJ (1990) Basic local alignment search tool. J Mol Biol 215:403–410PubMedGoogle Scholar
  2. Birladeanu L (2000) The story of the Wagner–Meerwein rearrangement. J Chem Ed 77:858–863CrossRefGoogle Scholar
  3. Duetz WA, Bouwmeester H, van Beilen JB, Witholt B (2003) Biotransformation of limonene by bacteria, fungi, yeasts, and plants. Appl Microbiol Biotechnol 61:269–277PubMedGoogle Scholar
  4. Eaton RW (2001) Plasmid-encoded phthalate catabolic pathway in Arthrobacter keyseri 12B. J Bacteriol 183:3689–3702PubMedCrossRefGoogle Scholar
  5. Eaton RW, Sandusky P (2009) Biotransformations of 2-methylisoborneol by camphor-degrading bacteria. Appl Environ Microbiol 75:583–588PubMedCrossRefGoogle Scholar
  6. Engle CE, Pounds GL, van der Ploeg M (1995) The cost of off-flavor. J World Aquac Soc 26:297–306CrossRefGoogle Scholar
  7. Finato B, Lorenzi R, Pelosi P (1992) Synthesis of new earthy odorants. J Agric Food Chem 40:857–859CrossRefGoogle Scholar
  8. Gunsalus IP, Marshall VP (1971) Monoterpene dissimilation: chemical and genetic models. Crit Rev Microbiol 1:291–310CrossRefGoogle Scholar
  9. IUPAC (1979) Section A-74. Bicyclic Terpenes. IUPAC Commission on Nomenclature of Organic Chemistry. Sections A, B, C, D, E, F, and H. Pergamon Press, Oxford.
  10. Jüttner F, Watson SB (2007) Biochemical and ecological control of geosmin and 2-methylisoborneol in source waters. Appl Environ Microbiol 73:4395–4406PubMedCrossRefGoogle Scholar
  11. March J (1992) Advanced organic chemistry, 4th edn. Wiley, New York, pp 1068–1072Google Scholar
  12. Martin JF, Bennett LW, Graham WH (1988a) Off-flavor in the channel catfish (Ictalurus punctatus) due to 2-methylisoborneol and its dehydration products. Wat Sci Technol 20:99–105Google Scholar
  13. Martin JF, Fisher TH, Bennett LW (1988b) Musty odor in chronically off-flavored channel catfish: isolation of 2-methylenebornane and 2-methyl-2-bornene. J Agric Food Chem 36:1257–1260CrossRefGoogle Scholar
  14. Mills OE, Chung S-Y, Johnsen PB (1993) Dehydration products of 2-methylisoborneol are not responsible for off-flavor in the channel catfish. J Agric Food Chem 41:1690–1692CrossRefGoogle Scholar
  15. Napolitano E, Giovani E, Ceccarelli N, Pelosi P (1996) Tertiary alcohols with earthy odor. J Agric Food Chem 44:2806–2809CrossRefGoogle Scholar
  16. Schumann R, Pendelton P (1997) Dehydration products of 2-methylisoborneol. Wat Res 31:1243–1246CrossRefGoogle Scholar
  17. Sumitomo H (1992) Biodegradation of 2-methylisoborneol by gravel sand filtration. Wat Sci Technol 25:191–198Google Scholar
  18. Tanaka A, Oritani T, Uehara F, Saito A, Kishita H, Niizeki Y, Yokota H, Fuchigami K (1996) Biodegradation of a musty odour component, 2-methylisoborneol. Water Res 30:759–761CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. (outside the USA) 2011

Authors and Affiliations

  1. 1.Southern Regional Research CenterAgricultural Research Service, U. S. Department of AgricultureNew OrleansUSA
  2. 2.New OrleansUSA

Personalised recommendations